| ST MARYS HOSPITAL OF ST MARYS COUNTY INC | $180,743,350 | $162,116,991 |
| ST MARYS NURSING CENTER INC | $15,175,220 | $14,275,558 |
| SOUTHERN MARYLAND REGIONAL LIBRARY ASSOCIATION INC | $3,309,593 | $2,959,950 |
| CEDAR LANE SENIOR LIVING COMMUNITY I INC | $1,587,064 | $1,792,636 |
| ST MARYS SUNSHINE CENTER INC | $933,581 | $1,114,296 |
| CEDAR LANE SENIOR LIVING COMMUNITY II INC | $910,136 | $909,016 |
| SOUTHERN MARYLAND RC AND D BOARD INC | $721,776 | $810,944 |
| LEONARDTOWN VOLUNTEER FIRE DEPARTMENT | $859,670 | $769,085 |
| ST MARYS COUNTY ADVANCED LIFE SUPPORT UNIT INC | $754,724 | $698,213 |
| SAINT MARYS COUNTY FAIR ASSOCIATION INC | $712,798 | $648,608 |
| CEDAR LANE SENIOR LIVING COMMUNITY III INC | $554,447 | $587,167 |
| VISIT ST MARYS MD INC | $496,261 | $582,918 |
| HOSPICE OF ST MARYS INC | $486,310 | $577,245 |
| WALDEN SIERRA CORPORATION | $166,789 | $471,611 |
| LEONARD HALL JUNIOR NAVAL ACADEMY INC | $313,982 | $309,116 |
| LEONARDTOWN VOLUNTEER RESCUE SQUAD INC | $432,576 | $305,072 |
| EDUCATION ASSOCIATION OF ST MARYS COUNTY | $290,960 | $282,549 |
| BOUNDLESS EXPECTATIONS INC | $220,045 | $240,328 |
| LEADERSHIP SOUTHERN MARYLAND INC | $189,386 | $204,011 |
| ST MARYS COUNTY ARTS COUNCIL INC | $167,790 | $183,392 |
| ON OUR OWN OF ST MARYS INC | $133,132 | $124,923 |
| CHESAPEAKE ORCHESTRA INC | $98,901 | $95,100 |
| UNITED WAY OF ST MARYS COUNTY MARYLAND INC | $121,150 | $94,663 |
| ST MARYS COUNTY HISTORICAL SOCIETY INC | $114,214 | $94,243 |
| SAINT MARYS GIRLS LACROSSE LEAGUE INC | $72,735 | $93,653 |